


In The Dead Of Night

by SinQueen69



Series: Requests [4]
Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Breeding Kink, Consensual Somnophilia, Creampie, Don't copy to another site, High School, Jock Derek Hale, Just the Tip, Knotting, M/M, Masturbation, Multiple Orgasms, Non-Consensual Somnophilia, Prompt Fill, Rape/Non-con Elements, Secret Slut Stiles Stilinski, Stalker Derek Hale, Stiles doesn’t know whose cum it is but he loves it, Teen Derek Hale, Teen Stiles Stilinski, Werewolf Derek Hale, anal gape, cum licking
Language: English
Status: Completed
Published: 2020-02-11
Updated: 2020-06-23
Packaged: 2021-02-28 04:21:33
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 3
Words: 2,872
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22667713
Author URL: https://archiveofourown.org/users/SinQueen69/pseuds/SinQueen69
Summary: Stiles wakes up, dripping cum and loves the fact he had no idea who came into his room that night to fuck him.Chapter 1- Prompt fill for Anon1Chapter 2- Anonymous requestChapter 3- Request Anon'sPLEASE READ THE TAGS AND THE STARTING AND CLOSING NOTES, PROCEED WITH CAUTION
Relationships: Derek Hale/Stiles Stilinski
Series: Requests [4]
Series URL: https://archiveofourown.org/series/1618726
Comments: 16
Kudos: 1689
Collections: Kelly's Picks





	1. Chapter 1

**Author's Note:**

> Prompt from Anonymous: 
> 
> Stiles fantasizes about someone coming inside his room and fucking him. But he's not sure if it's a dream anymore when he wakes up on his stomach, ass filled to the brim with cum. He thinks it's Scott since they fool around sometimes. But it could be his Dad who can come in and out his room anytime. Then again he doesn't lock his windows it could be anyone. It's driving him nuts.
> 
> Derek slips in Stiles room and masturbates at the boy's vulnerable position. He pushes just this tip of his cock, coming inside the boy. One of these days, he will fuck him for real. But not right now.
> 
> Highschool AU. Werewolf!Derek. Jock!Derek. SecretSlut!Stiles.

Stiles yawned before he even opened his mouth. He squirmed from where he was lying on his stomach, his stomach felt full and rather bloated. Stiles opened his eyes and rolled over onto his side before gasping when something slick and wet slipped down his thighs. Stiles reached between his thighs and moaned as he ran his thumbs over thick rivers of cum and how his hole was slightly loose. 

Stiles felt his cheeks burn but a huge smile spread over his lips as he clenched up before he rolled off of his bed. Stiles hurried over to his mirror and twisted around, prying his ass cheeks apart and relaxed. Stiles moaned outright as he watched the thick, white cum ooze out of his pink hole. Stiles’ cock stiffened up as he watched as the cum stained his thighs and he traced his full hole with his fingers.

“I wonder whose it is, fuck this is so hot,” Stiles muttered as he plunged two of his fingers into his cum-drenched hole in a well-practiced move. Stiles moaned at the lewd squelch of the cum and gripped his hard cock and began to stroke himself quickly as his mind wandered. 

Maybe it had been Scott, the two had been fooling around lately and he knew about this fantasy of his. Maybe it was something at school, Stiles’ didn’t care as his orgasm washed over him, his cum spilling over his fingers with embarrassing ease. 

“Fuck,” Stiles whispered as he caved and stuck his cum-coated fingers into his mouth and whimpered, as he tasted the unknown man’s cum. 

Stiles knelt there awkwardly for a few more moments as he suckled at his fingers and clenched and unclenched his hole to just feel the cum inside of him and the knowledge that he had no idea whose it was. 

~~//~~

Derek Hale leaned against his locker in school that morning, his eyes locked on Stiles. His inner wolf was preening; he could smell his scent all over the other teen. He watched as Stiles with almost glowing eyes as he enjoyed the way their scents mingled from his actions the previous night. He hadn’t meant to overhear what Stiles had told Scott, but he had and he fought for weeks against doing what Stiles told Scott. Finally, he gave in and went to Stiles’ house the other night.

Derek ducked into the bathroom, thankful for his lunch break and that the bathroom was empty. Derek locked the door and sat down on the toilet as he unzipped his jeans. Derek sighed as he took his hardening cock into his hand and gave himself a rough stroke to smear the building pre-cum over the length of his cock. 

Derek tipped his head back and remembered the other night in Stiles' room and tightened his grip on his cock. 

~~//~~

Derek slipped through the open window of Stiles’ bedroom and had to instantly cup his cock through his sweatpants at the sight that greeted him. Stiles looked like the usual nerd at school, but here his true self was obvious. Stiles was sprawled out on his bed above his sheets, completely naked and laid out like an offering. 

Derek’s eyes glowed in the darkness of the room as he stepped closer. Derek smiled sharply as he noticed how Stiles’ legs were spread wide; even in sleep, his body was showing Stiles’ true self. Derek lightly trailed his fingertips over Stiles’ balls and soft cock that was pressed against the mattress below him and smirked when Stiles mumbled and shifted, his knees bending a bit and the new position propped Stiles’ plump ass up higher. 

Derek kept his touch feather-light and went slow but he managed to tug those tempting cheeks apart to get a good look at the teen’s tight, pink pucker. Derek licked his lips as his cock throbbed and pushed against the fabric of his sweatpants, it was perfect and Derek wanted nothing more than to watch it open up for his cock. That was for another night, he had to bide his time for that, let Stiles’ body get adjusted to his cock. 

Derek released Stiles' cheeks and knelt in the space Stiles’ legs had created for him and tugged his sweatpants down until just his cock and balls were exposed. The head of Derek’s cock was wet with pre-cum and Derek used it to wet his shaft before he began to jerk himself off, not looking away from Stiles’ offered ass and the thought of burying himself deep in the teen’s pretty hole. 

Derek wondered if Stiles’ stomach would be bugling when he finally took Derek’s cock, he wondered if his slim stomach would be swollen and pregnant looking with his cum. Derek smothered a moan at the mental image and the fact that in each of these images, Stiles was still fast asleep but his body so eager for it. 

Derek couldn’t stop himself and guided his cock forward and he didn’t stop until Stiles’ ass cheeks were once again held apart and Derek was hissing quietly as he pushed the fat head of his cock into the teen’s tight hole and it took everything he had to stop himself from just plowing into that tight, welcoming heat. Stiles just made a snuffling noise before falling silent in his deep sleep. 

Derek just stared at the way Stiles’ rim expanded around the tip of his cock and Derek couldn’t help but stroke his shaft, needing to come, needing to come inside of Stiles. Derek tossed his head back and swallowed a moan, not wanting Stiles to wake up. Derek’s hand curled tighter and he shuddered as his orgasm hit him and he pumped Stiles’ body full of his large load of cum. 

~~//~~

Derek jolted out of his memory and slapped a hand over his mouth to muffle his groan as his cum spurted over his hand and he panted for breath. He had come just as hard as he had the previous night just inside of Stiles’ hot, tight hole. Fuck if he couldn’t wait to do it again, maybe giving Stiles another inch of his cock this time and Derek smiled as his wolf made a pleased noise.

**Notes for the Chapter:**

> Trigger Warnings:  
> Rape/Non-Con.  
> Stiles doesn't know who came in him, he loves it but it still non-con  
> Derek is a total werewolf stalker and did rape him by coming in Stiles while the teen was asleep.


	2. Chapter 2

**Summary for the Chapter:**

> Anonymous from my request form wanted: How about Derek coming for round 2 and Stiles waking up just seconds before Derek cums?

Derek found himself scaling Stiles’ house again, slipping into the other teen’s window before he knew what he was doing. His body did as his cock pushed against the fabric of his sweatpants and his inner wolf was getting excited at the sight of Stiles, laid out naked on top of his covers again. Stiles was deep asleep and obvious to the world around him and Derek was settling on the end of the bed, eyes glowing as he stared at Stiles’ ass, remembering the tight heat that the tip of his cock had been able to enjoy last time. 

Derek had waited until he was sure the Sheriff was working the night shift so as long as Stiles didn’t wake up then he wouldn’t be caught. Derek pushed his sweatpants down around his thighs and stroked his cock, smearing the copious amounts of pre-cum over the hard shaft. He didn’t pay the same kind of attention to Stiles’ body this time, all he has wanted since the last time was to be buried inside of his classmate’s tight hole and claim him again. 

Derek cupped Stiles’ plump ass cheeks and parted them, swallowing a groan at how Stiles’ was already wet with lube and his rim puffy. The teen had been playing with himself before he fell asleep and Derek was glad he had chosen that night to come over. Derek dipped the tips of his thumbs into the other’s hole and tugged, rumbling quietly when the teen’s rim stretched under the pressure with ease. 

Derek licked his lips as he shuffled close enough to shift his hips to settle the head of his cock against Stiles’ stretched rim. Derek rumbled again in place of a moan as Stiles’ hole swallowed up the tip of his cock just as nicely as the first time. Derek risked it and inched a bit more of his cock into the sleeping teen below him and had to cover his mouth with his hand to stop himself from letting out a loud moan as his cock slid in with ease. 

Derek placed his hand on the bed by Stiles’ hip as he bent over Stiles back, moving his hips so more of his cock could push deeper into Stiles. Stiles mewled in his sleep as he shuffled underneath Derek, showing signs of slowly waking up but Derek found he didn’t care as his balls settled against Stiles’ ass, his cock fully sheathed inside of the sleeping teen in the way he had wanted since the first night. 

Derek rocked his hips a few time, watching his cock slide in and out of Stiles’ loose rim, it was entrancing and Derek knew he wasn’t going to last much longer.

“Mmm, oh fuck, Derek?” Stiles sleepy voice pierced Derek’s haze of pleasure. Stiles and Derek locked eyes with each other, but Derek kept up his steady pace, watching as Stiles face was covered with pleasure and a whine escaped his mouth.

“Fuck, keep going!” Stiles encouraged, getting his knees up under him to push back to meet Derek’s thrusts with his own. 

“I’m going to come in you again Stiles,” Derek warned, uncaring that his eyes were glowing as his wolf clawed at the surface.

“Yes, yes, come in me, mark me!” Stiles moaned as he reached between his thighs to jerk himself off as Derek buried his cock deep in his ass. Stiles keened as he felt Derek’s hot cum begin to blood into him as his classmate emptied his balls into him and Stiles came the moment Derek pulled out, allowing a glob of his cum to slip out of Stiles’ slightly gaping ass. 

Stiles collapsed onto his bed, breathing heavily and he turned his head to look back at Derek whose cheeks were flushed and cock limp between his thighs. 

“You can come by any time you know, awake or asleep I’d love to take your cock and cum again.” Stiles murmured as exhaustion took him over again and he smiled when he felt Derek brush his fingers over his cheek before he fell back asleep, content and full of Derek’s cum. 

Derek let out a small puff of air as Stiles fell back asleep and he tugged Stiles’ cheeks apart to stare at the way his cum slowly dripped out of the teen’s hole and his inner wolf crooned happily at the sight. Derek smiled at Stiles’ sleeping face before he settled his sweatpants back into place, content for the time being with the permission Stiles gave him burning in the back of his mind.


	3. Chapter 3

**Summary for the Chapter:**

> In The Dead of Night   
> Chapter 3 – Final
> 
> Anon on tumblr: I love In the Dead of Night - somnophilia (whatever the level of consent) is one of my favorite kinks. Now that Stiles knows it was Derek, I'd love to see a whole weekend or something where his dad is away and Derek has him stay in bed and just uses him whenever he wants, asleep or awake. Size kink and come inflation are also in my top kinks. Thanks for this series! It's so hot and I love the variety of stories.
> 
> +
> 
> Request Form Anon: You can choose any werewolf you want but with Stiles as the bottom. The werewolf want to see how many knots Stiles can take and Stiles agrees to let the werewolf fuck him for however long it takes to hit the limit for both of them. So they sex and Stiles starts to fall asleep but he lets the werewolf fuck him while he is sleeping too. When stiles wakes up the werewolf is sleeping and Stiles looks and sees that he is filled so much and is turned on which wake the werewolf up and they start fucking again.

**Notes for the Chapter:**

> This shall be the last chapter of this fic, I hope you enjoy!

“Ready?” Stiles wiggled his eyebrows as he took the glass of water from the older teen. 

“You’re sure about this?” Derek was all but vibrating in excitement, his cock already standing tall from his groin. Stiles’ father was away for the weekend for a conference and Derek planned on spending the night with his new boyfriend, ready to indulge in the kinks that had brought them together. 

Stiles downed a sleeping pill with a gulp of water and smirked at the older teen who huffed out a laugh at the obvious answer. Derek leaned in and kissed the younger teen soundly, laying Stiles’ naked body down onto the bed. Derek slotted himself between Stiles’ pale thighs, rutting his cock between Stiles’ ass cheeks in excitement. 

“If you want me to feel your first knot you better hurry sour wolf,” Stiles yawned as he lifted his legs up to drape them around the werewolf’s hips. 

Derek didn’t waste any time, he was so turned on his cock was starting to hurt. Stiles gave a low moan as the older teen pushed into him meeting no resistance, after all, Stiles was diligent about keeping himself wet and open in case Derek felt the need to fuck him. 

Derek ducked his face against Stiles’ throat as he gave fast, sloppy thrusts. He didn’t have to draw this out, he had all night to take his time and he wanted Stiles to fall asleep with his knot deep inside of him. Derek growled at the thought and put more force behind his thrusts. Derek groaned as he came quickly, his knot popping inside of Stiles’ rim, locking them together and Stiles made a choked noise.

“Fuck, yes.” Stiles’ words trailed off and Derek lifted his head and grinned at the sight of Stiles’ eyes closed and face slack in sleep. Derek rolled his hips, shifting his knot and all he got from Stiles was a sleepy smacking of his lips and Derek knew the sleeping pill was working its magic. 

Derek stayed in his position sprawled on top of Stiles, pumping him full of cum until his knot went down enough for him to pull out. Derek lifted Stiles’ limp legs in order to get a better view of Stiles’ hole and was not disappointed. Stiles’ rim was already loose and puffy from Derek’s first knot and oozing thick white cum. 

Derek kept Stiles’ legs held high and slotted his cock into Stiles’ messy hole again, licking his lips at the sight of his cum being forced both deeper into and out of Stiles’. Stiles’ head lolled to the side as he breathed evenly as Derek began to thrust in and out of him using his cum as lube. Derek couldn’t take his eyes away from the way Stiles’ hole looked as his cock moved in and out of it. 

Derek put Stiles’ legs over his shoulders, planting his hands on the bed on either side of the younger teen and began to thrust deep and hard into Stiles’. Stiles moaned in his sleep, eyes moving under his eyelids and Derek kissed those tempting lips before sucking his way down Stiles’ throat and left a massive mark on the teen’s collarbone. 

Derek groaned he felt his knot starting to swell again; it was always easier to knot again once the first one was out of the way. Derek placed his hand on Stiles’ stomach and groaned in pleasure as he felt the teen’s skin start to bulge and distend as the werewolf’s knot jumped to full size. Derek leaned up to look at the obscene way Stiles’ stomach looked as Derek began to pump another large load of cum into the sleeping teen. 

Derek swore under his breath at the sight, searing it into his memory forever. Stiles’ cock gave short spurts of cum as the teen orgasmed in his sleep from having Derek’s knot pressed firmly against his prostate. 

Derek shallowly fucked the sleeping teen with his knot, forcing more of his cum to seep out of Stiles’ stuffed hole and dribbles of cum to spurt from Stiles’ cock. 

Derek grinned as he pulled out when his knot deflated again and flipped the teen onto his stomach before slamming back into the teen’s sloppy hole. Stiles moaned into the pillow, his arms and legs splayed every which way and more cum was being pushed out of his hole around Derek’s cock by the way he was laying on his come filled stomach. 

Derek didn’t care as he plunged his cock into the sleeping teen’s warm, soaked hole as he tossed his head back with a long moan as he used Stiles’ unresponsive body to find his third release of the night, knot popping into Stiles’ gaping hole with ease by this point. 

~~//~~

Stiles squeezed his eyes as he slowly roused himself from his drug-induced sleep. Stiles was on his back, feeling heavy and achy in the most wonderful way. Stiles opened his eyes and peered down at his body. The teen’s usually flat stomach was swollen and so full he looked like he had a baby bump, dry pools of cum decorated the skin and Stiles’ limp cock was lying against his thigh. 

Stiles smiled as he reached past his extended stomach and his fingers brushed through a massive amount of cum fresh and dry on his thighs before he sank two fingers into his ass. 

“Oh yes,” Stiles shuddered in pleasure at the feeling of the thick cum filling his sore hole, Stiles tested the waters and moaned when he easily added his ring and pinkie fingers into his gaping hole.

Stiles fingered his messy, well-used hole for a little bit while he turned his head to the side to see Derek totally conked out, looking exhausted but stated. Stiles grinned; this had been such a good idea. Derek mumbled in his sleep, turning onto his side so he was facing Stiles. Stiles turned slowly so his ass was facing the older teen. 

Stiles removed his fingers and used his wet fingers to guide the sleeping werewolf’s soft cock into his hole. Stiles panted at the lewd squelching noise as Derek’s cock entered him, Stiles kept moving until he could feel the older teen’s balls settle against his ass. Stiles closed his eyes and decided to get some more sleep, using his sloppy hole to keep the werewolf’s cock warm in the meantime.

**Author's Note:**

> Trigger Warnings:  
> Rape/Non-Con.  
> Stiles doesn't know who came in him, he loves it but it still non-con  
> Derek is a total werewolf stalker and did rape him by coming in Stiles while the teen was asleep.


End file.
